The present invention relates to salicylic acid derivatives of the formula I 
where the index and the substituents are as follows:
X is halogen, NO2, cyano, C1-C4-alkyl or C1-C4-alkoxy;
m is 0, 1, 2 or 3, it being possible for the substituents X to differ from each other if n is greater than 1;
A is OH, C1-C4-alkoxy, NH2, NHCH3 or N(CH3)2;
R1 is phenyl, naphthyl, C3-C10-cycloalkyl, 5-membered or 6-membered hetaryl or 5-membered or 6-membered heterocyclyl containing one to three N atoms and/or one O or S atom or one or two O and/or S atoms, the ring systems being unsubstituted or substituted by one to three radicals Ra:
Ra is cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkyloxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy, C(xe2x95x90NORxcex1)xe2x80x94ORxcex2 or OC(Rxcex1)2xe2x80x94C(Rxcex2)xe2x95x90NORxcex2,
xe2x80x83the cyclic radicals, in turn, being unsubstituted or substituted by one to three radicals Rb:
Rb is cyano, nitro, halogen, hydroxyl, amino, aminocarbonyl, aminothiocarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C1-C6-alkylaminothiocarbonyl, di-C1-C6-alkylaminothiocarbonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy or C(xe2x95x90NORxcex1)xe2x80x94ORxcex2;
xe2x80x83Rxcex1, Rxcex2 is hydrogen or C1-C6-alkyl;
R2 is hydrogen, cyano, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-alkylthio,
xe2x80x83the hydrocarbon radicals being unsubstituted or partially or fully halogenated or it being possible for them to have attached to them one to three groups Rc:
Rc is halogen, cyano, nitro, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino,
xe2x80x83di-C1-C6-alkylamino, C2-C6-alkenyl, C3-C6-alkenyloxy, C3-C6-alkynyloxy or C1-C4-alkylenedioxy which can be halogenated.
Furthermore, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling harmful fungi.
WO-A 97/08135, DE-A 197 10 609 and WO-A 99/27783 disclose acylaminosalicylamides for controlling harmful fungi.
However, their action is unsatisfactory in many cases.
It is an object of the invention to provide compounds with an improved action.
We have found that this object is achieved by the compounds defined at the outset. Moreover, there have been found processes for their preparation, compositions comprising them and methods of controlling phytopathogenic harmful fungi using the compounds I.
The compounds of the formula I differ from those of the prior art by the hydrazide group.
The compounds of the formula I show an increased efficacy against harmful fungi compared with the known compounds.
Compounds of the formula I can be prepared for example starting from alkyl salicylates of the formula II where A is C1-C4-alkoxy and Z is a protecting group which can be eliminated under acidic conditions, such as, for example, an acetyl group.
Compounds of the formula II can be obtained by free-radical halogenation under generally customary conditions, especially advantageously by bromination with N-bromosuccinimide (NBS) using azobisisobutyronitrile (AIBN) as free-radical initiator with exposure to light [cf. J. Amer. Chem. Soc., Vol. 71 (1949), p. 2137 et seq; ibid., Vol. 90 (1968), p. 1797 et seq]. Compounds of the formula II where A is methoxy, Z is acetyl and Hal is bromine are preferred. 
This reaction is usually carried out at temperatures of from 20xc2x0 C. to 150xc2x0 C., preferably from 50xc2x0 C. to 100xc2x0 C., in an inert organic solvent [cf. Can. J. Chem., Vol. 33 (1955), p. 1819; J. Org. Chem., Vol. 49 (1984), p. 2158].
Suitable solvents are halogenated hydrocarbons such as carbon tetrachloride, chloroform and chlorobenzene. Mixtures of the solvents mentioned may also be used.
In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ NBS in an excess based on II.
The starting materials II required for the preparation of the compounds I are commercially available, known from the literature [Bull. Soc. Chim. Fr., Vol. 9 (1966), p. 2821; Biotechnol. Lett., Vol. 15 (1993), p. 469; J. Fluorine Chem., Vol. 74 (1995), p. 69] or can be prepared in accordance with the literature cited.
The dihalo compounds of the formula III are oxidized with elimination of the protecting group Z under acidic conditions to give the keto compounds IV. 
This reaction is usually carried out at temperatures of from 20xc2x0 C. to 150xc2x0 C., preferably from 20xc2x0 C. to 100xc2x0 C., in an inert organic solvent in the presence of an acid (cf. Org. Synth., Vol. 20 (1940), p. 92].
Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide, especially preferably methanol, ethanol and n-propanol. Mixtures of the solvents mentioned may also be used.
Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, aqueous hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid.
In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as solvents.
To prepare compounds I where A is NH2, NHCH3 or N(CH3)2, salicylic esters IV are reacted with ammonia or methylamine to give salicylamides of the formula IV.1 where R3 is hydrogen or methyl; the reaction with dimethylamine gives compounds of the formula IV.3:
This reaction is usually carried out at temperatures of from 20xc2x0 C. to 150xc2x0 C., preferably from 20xc2x0 C. to 100xc2x0 C., in an inert organic solvent [cf. Arch. Pharm. (1982), p. 941].
Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile, alcohols, and dimethyl sulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide, especially preferably N,N-dimethylformamide and N,N-dimethylacetamide. Mixtures of the solvents mentioned may also be used.
In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ the amine in an excess based on IV. 
The imino group is usually eliminated from IV.1 at temperatures of from 20xc2x0 C. to 150xc2x0 C., preferably from 20xc2x0 C. to 100xc2x0 C., in an inert organic solvent in the presence of an acid [cf. J. Chem. Soc. (1957), p. 3807; J. Org. Chem., Vol. 6 (1941), p. 489].
Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide, especially preferably methanol, ethanol and n-propanol. Mixtures of the solvents mentioned may also be used.
Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, aqueous hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid. 
To prepare compounds of the formula I where A is hydroxyl, the alkyl esters of the formula IV are hydrolyzed by customary methods to give the salicylic acids of the formula IV.4 [cf. Organikum [Organic chemistry], 16th Ed., pp. 415 and 622, VEB Deutscher Verlag der Wissenschaften, Berlin 1985]. This reaction is usually carried out at temperatures of from 10xc2x0 C. to 80xc2x0 C., preferably 20xc2x0 C. to 60xc2x0 C., in an inert organic solvent in the presence of a base, such as alkali metal hydroxides or alkaline earth metal hydroxides, in particular sodium hydroxide or potassium hydroxide.
Depending on the form which radical A in formula I takes, compounds of the formulae IV, IV.2, IV.3 or IV.4 are reacted with hydrazides of the formula V to give compounds of the formula I. 
This reaction is usually carried out at temperatures of from 20xc2x0 C. to 150xc2x0 C., preferably from 20xc2x0 C. to 80xc2x0 C., in an inert organic solvent in the presence of an acid [cf. Org. Prep. Proced. Int., Vol. 30 (1998), p. 177; CH-A 661 276].
Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, ethers, nitrites, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and dimethyl sulfoxide, N,N-dimethylformamide and N,N-dimethylacetamide, especially preferably methanol, ethanol, n-propanol, isopropanol or N,N-dimethylformamide. Mixtures of the solvents mentioned may also be used.
Acids and acidic catalysts which are used are inorganic acids such as hydrofluoric acid, aqueous hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid.
In general, the acids are employed in catalytic amounts, but they may also be used in equimolar amounts, in an excess or, if appropriate, as solvents.
In general, the starting materials are reacted with each other in equimolar amounts. It may be advantageous for the yield to employ V in an excess based on IV.
The reaction mixtures are worked up in the customary manner, for example by mixing with water, phase separation and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or pale brown, viscous oils which are purified or freed from volatile components under reduced pressure and at a moderately elevated temperature. If the intermediates and end products are obtained as solids, they may also be purified by recrystallization or digestion.
If individual compounds I cannot be obtained by the above-described routes, they can be prepared by derivatizing the compounds I.
Upon their preparation, the compounds I may be obtained, owing to their Cxe2x95x90C and Cxe2x95x90N double bonds, as E/Z isomer mixtures which can be separated in the customary manner, for example by crystallization or chromatography, to give the individual compounds.
If, upon synthesis, isomer mixtures are obtained, separation is, however, not absolutely necessary since some of the individual isomers may be converted into each other during preparation for use, or upon use (for example with exposure to light, acids or bases). Similar conversions may also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
In the definitions of the symbols in the above formulae, collective terms were used which generally represent the following substituents:
halogen: fluorine, chlorine, bromine and iodine;
alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4 or 6 carbon atoms, for example C1-C6-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C1-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (xe2x80x94Oxe2x80x94);
alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4 or 6 carbon atoms and one double bond in any position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4 or 6 carbon atoms and one triple bond in any position, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
cycloalkyl: monocyclic, saturated hydrocarbon groups having 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
5- or 6-membered heterocyclyl contains, in addition to carbon ring members, one to three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;
5-membered heteroaryl contains one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl ring groups which may contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, e.g. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
6-membered heteroaryl contains one to three, or one to four, nitrogen atoms: 6-membered heteroaryl ring groups which, in addition to carbon atoms, may contain one to three, or one to four, nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl;
alkylene: divalent unbranched chains of 1 to 4 CH2 groups, e.g. CH2, CH2CH2, CH2CH2CH2 and CH2CH2CH2CH2;
alkylenedioxy: divalent unbranched chains of 1 to 3 CH2 groups, both valences being bonded to the skeleton by an oxygen atom, e.g. OCH2O, OCH2CH2O and OCH2CH2CH2O.
Especially preferred with regard to the intended use of the salicylic acid derivatives of the formula I are the following meanings of the substituents, in each case alone or in combination:
Especially preferred are compounds of the formula I where A is methyl, methoxy, hydroxyl, amino and methylamino.
Particularly preferred are compounds IA: 
In addition, especially preferred compounds I are those where the index m is zero; these compounds are described by the formula IB: 
Especially preferred compounds I are furthermore those where R2 is methyl.
Moreover, especially preferred compounds I are those where (X)m is in the para position relative to the phenol OH group and is halogen, NO2, CN and C1-C4-alkoxy, in particular 4-chloro, 4-bromo and 4-NO2.
Particularly preferred compounds I are also those where R1 is cyclohexyl and phenyl which is unsubstituted or substituted by one to three radicals Ra, particularly phenyl. In the case of compounds where R1 is cyclohexyl, the substituent Ra may be in the E- or Z-position relative to the Cxe2x80x94R1 bond.
Especially preferred compounds I are those where R1 is pyrazole, pyrimidine, pyridine, pyrazine and thiophene, each of which is unsubstituted or substituted by one to three radicals Ra.
Also preferred are compounds I where Ra is chlorine, bromine, nitro, cyano, methyl, ethyl, n- and iso-propyl, n- and sec- and tert-butyl and phenyl, the aromatic ring being unsubstituted or substituted by one or two radicals from the group consisting of chlorine, bromine, nitro, cyano and methyl.
Equally especially preferred are compounds I where R2 is hydrogen, methyl, methoxy and cyano, in particular hydrogen and methyl.
The especially preferred embodiments of the intermediates with regard to the variables correspond to those of radicals A, (X)m, R1 and R2 of the formula I.
Particularly preferred with regard to their use are the compounds I which are compiled in the tables which follow. In addition, the groups mentioned in the tables for a substituent constitute an especially preferred embodiment of the substituent in question, independently of the combination in which they are mentioned.
Table 1
Compounds of the formula I where m is zero, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A 
Table 2
Compounds of the formula I where m is zero, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 3
Compounds of the formula I where m is zero, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 4
Compounds of the formula I where m is zero, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 5
Compounds of the formula I where (X)m is 3-chloro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 6
Compounds of the formula I where (X)m is 3-chloro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 7
Compounds of the formula I where (X)m is 3-chloro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 8
Compounds of the formula I where (X)m is 3-chloro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 9
Compounds of the formula I where (X)m is 4-chloro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 10
Compounds of the formula I where (X)m is 4-chloro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 11
Compounds of the formula I where (X)m is 4-chloro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 12
Compounds of the formula I where (X)m is 4-chloro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 13
Compounds of the formula I where (X)m is 5-chloro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 14
Compounds of the formula I where (X)m is 5-chloro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 15
Compounds of the formula I where (X)m is 5-chloro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 16
Compounds of the formula I where (X)m is 5-chloro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 17
Compounds of the formula I where (X)m is 3-bromo, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 18
Compounds of the formula I where (X)m is 3-bromo, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 19
Compounds of the formula I where (X)m is 3-bromo, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 20
Compounds of the formula I where (X)m is 3-bromo, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 21
Compounds of the formula I where (X)m is 4-bromo, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 22
Compounds of the formula I where (X)m is 4-bromo, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 23
Compounds of the formula I where (X)m is 4-bromo, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 24
Compounds of the formula I where (X)m is 4-bromo, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 25
Compounds of the formula I where (X)m is 5-bromo, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 26
Compounds of the formula I where (X)m is 5-bromo, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 27
Compounds of the formula I where (X)m is 5-bromo, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 28
Compounds of the formula I where (X)m is 5-bromo, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 29
Compounds of the formula I where (X)m is 3-nitro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 30
Compounds of the formula I where (X)m is 3-nitro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 31
Compounds of the formula I where (X)m is 3-nitro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 32
Compounds of the formula I where (X)m is 3-nitro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 33
Compounds of the formula I where (X)m is 4-nitro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 34
Compounds of the formula I where (X)m is 4-nitro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 35
Compounds of the formula I where (X)m is 4-nitro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 36
Compounds of the formula I where (X)m is 4-nitro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 37
Compounds of the formula I where (X)m is 5-nitro, A is methoxy and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 38
Compounds of the formula I where (X)m is 5-nitro, A is methoxy and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 39
Compounds of the formula I where (X)m is 5-nitro, A is methoxy and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 40
Compounds of the formula I where (X)m is 5-nitro, A is methoxy and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 41
Compounds of the formula I where m is zero, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 42
Compounds of the formula I where m is zero, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 43
Compounds of the formula I where m is zero, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 44
Compounds of the formula I where m is zero, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 45
Compounds of the formula I where (X)m is 3-chloro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 46
Compounds of the formula I where (X)m is 3-chloro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 47
Compounds of the formula I where (X)m is 3-chloro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 48
Compounds of the formula I where (X)m is 3-chloro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 49
Compounds of the formula I where (X)m is 4-chloro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 50
Compounds of the formula I where (X)m is 4-chloro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 51
Compounds of the formula I where (X)m is 4-chloro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 52
Compounds of the formula I where (X)m is 4-chloro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 53
Compounds of the formula I where (X)m is 5-chloro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 54
Compounds of the formula I where (X)m is 5-chloro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 55
Compounds of the formula I where (X)m is 5-chloro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 56
Compounds of the formula I where (X)m is 5-chloro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 57
Compounds of the formula I where (X)m is 3-bromo, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 58
Compounds of the formula I where (X)m is 3-bromo, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 59
Compounds of the formula I where (X)m is 3-bromo, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 60
Compounds of the formula I where (X)m is 3-bromo, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 61
Compounds of the formula I where (X)m is 4-bromo, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 62
Compounds of the formula I where (X)m is 4-bromo, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 63
Compounds of the formula I where (X)m is 4-bromo, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 64
Compounds of the formula I where (X)m is 4-bromo, A is amino and R2 is isopropyl, and the radical R1 for each compound corresponds to one line of Table A
Table 65
Compounds of the formula I where (X)m is 5-bromo, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 66
Compounds of the formula I where (X)m is 5-bromo, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 67
Compounds of the formula I where (X)m is 5-bromo, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 68
Compounds of the formula I where (X)m is 5-bromo, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 69
Compounds of the formula I where (X)m is 3-nitro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 70
Compounds of the formula I where (X)m is 3-nitro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 71
Compounds of the formula I where (X)m is 3-nitro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 72
Compounds of the formula I where (X)m is 3-nitro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 73
Compounds of the formula I where (X)m is 4-nitro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 74
Compounds of the formula I where (X)m is 4-nitro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 75
Compounds of the formula I where (X)m is 4-nitro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 76
Compounds of the formula I where (X)m is 4-nitro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 77
Compounds of the formula I where (X)m is 5-nitro, A is amino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 78
Compounds of the formula I where (X)m is 5-nitro, A is amino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 79
Compounds of the formula I where (X)m is 5-nitro, A is amino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 80
Compounds of the formula I where (X)m is 5-nitro, A is amino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 81
Compounds of the formula I where m is zero, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 82
Compounds of the formula I where m is zero, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 83
Compounds of the formula I where m is zero, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 84
Compounds of the formula I where m is zero, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 85
Compounds of the formula I where (X)m is 3-chloro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 86
Compounds of the formula I where (X)m is 3-chloro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 87
Compounds of the formula I where (X)m is 3-chloro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 88
Compounds of the formula I where (X)m is 3-chloro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 89
Compounds of the formula I where (X)m is 4-chloro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 90
Compounds of the formula I where (X)m is 4-chloro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 91
Compounds of the formula I where (X)m is 4-chloro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 92
Compounds of the formula I where (X)m is 4-chloro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 93
Compounds of the formula I where (X)m is 5-chloro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 94
Compounds of the formula I where (X)m is 5-chloro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 95
Compounds of the formula I where (X)m is 5-chloro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 96
Compounds of the formula I where (X)m is 5-chloro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 97
Compounds of the formula I where (X)m is 3-bromo, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 98
Compounds of the formula I where (X)m is 3-bromo, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 99
Compounds of the formula I where (X)m is 3-bromo, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 100
Compounds of the formula I where (X)m is 3-bromo, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 101
Compounds of the formula I where (X)m is 4-bromo, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 102
Compounds of the formula I where (X)m is 4-bromo, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 103
Compounds of the formula I where (X)m is 4-bromo, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 104
Compounds of the formula I where (X)m is 4-bromo, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 105
Compounds of the formula I where (X)m is 5-bromo, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 106
Compounds of the formula I where (X)m is 5-bromo, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 107
Compounds of the formula I where (X)m is 5-bromo, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 108
Compounds of the formula I where (X)m is 5-bromo, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 109
Compounds of the formula I where (X)m is 3-nitro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 110
Compounds of the formula I where (X)m is 3-nitro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 111
Compounds of the formula I where (X)m is 3-nitro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 112
Compounds of the formula I where (X)m is 3-nitro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 113
Compounds of the formula I where (X)m is 4-nitro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 114
Compounds of the formula I where (X)m is 4-nitro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 115
Compounds of the formula I where (X)m is 4-nitro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 116
Compounds of the formula I where (X)m is 4-nitro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 117
Compounds of the formula I where (X)m is 5-nitro, A is methylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 118
Compounds of the formula I where (X)m is 5-nitro, A is methylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 119
Compounds of the formula I where (X)m is 5-nitro, A is methylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 120
Compounds of the formula I where (X)m is 5-nitro, A is methylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 121
Compounds of the formula I where m is zero, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 122
Compounds of the formula I where m is zero, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 123
Compounds of the formula I where m is zero, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 124
Compounds of the formula I where m is zero, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 125
Compounds of the formula I where (X)m is 3-chloro, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 126
Compounds of the formula I where (X)m is 3-chloro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 127
Compounds of the formula I where (X)m is 3-chloro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 128
Compounds of the formula I where (X)m is 3-chloro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 129
Compounds of the formula I where (X)m is 4-chloro, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 130
Compounds of the formula I where (X)m is 4-chloro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 131
Compounds of the formula I where (X)m is 4-chloro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 132
Compounds of the formula I where (X)m is 4-chloro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 133
Compounds of the formula I where (X)m is 5-chloro, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 134
Compounds of the formula I where (X)m is 5-chloro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 135
Compounds of the formula I where (X)m is 5-chloro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 136
Compounds of the formula I where (X)m is 5-chloro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 137
Compounds of the formula I where (X)m is 3-bromo, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 138
Compounds of the formula I where (X)m is 3-bromo, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 139
Compounds of the formula I where (X)m is 3-bromo, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 140
Compounds of the formula I where (X)m is 3-bromo, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 141
Compounds of the formula I where (X)m is 4-bromo, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 142
Compounds of the formula I where (X)m is 4-bromo, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 143
Compounds of the formula I where (X)m is 4-bromo, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 144
Compounds of the formula I where (X)m is 4-bromo, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 145
Compounds of the formula I where (X)m is 5-bromo, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 146
Compounds of the formula I where (X)m is 5-bromo, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 147
Compounds of the formula I where (X)m is 5-bromo, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 148
Compounds of the formula I where (X)m is 5-bromo, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 149
Compounds of the formula I where (X)m is 3-nitro, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 150
Compounds of the formula I where (X)m is 3-nitro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 151
Compounds of the formula I where (X)m is 3-nitro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 152
Compounds of the formula I where (X)m is 3-nitro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 153
Compounds of the formula I where (X)m is 4-nitro, A and R2 are hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 154
Compounds of the formula I where (X)m is 4-nitro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 155
Compounds of the formula I where (X)m is 4-nitro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 156
Compounds of the formula I where (X)m is 4-nitro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 157
Compounds of the formula I where (X)m is 5-nitro, A is dimethylamino and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 158
Compounds of the formula I where (X)m is 5-nitro, A is dimethylamino and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 159
Compounds of the formula I where (X)m is 5-nitro, A is dimethylamino and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 160
Compounds of the formula I where (X)m is 5-nitro, A is dimethylamino and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 161
Compounds of the formula I where m is zero, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 162
Compounds of the formula I where m is zero, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 163
Compounds of the formula I where m is zero, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 164
Compounds of the formula I where m is zero, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 165
Compounds of the formula I where (X)m is 3-chloro, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 166
Compounds of the formula I where (X)m is 3-chloro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 167
Compounds of the formula I where (X)m is 3-chloro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 168
Compounds of the formula I where (X)m is 3-chloro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 169
Compounds of the formula I where (X)m is 4-chloro, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 170
Compounds of the formula I where (X)m is 4-chloro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 171
Compounds of the formula I where (X)m is 4-chloro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 172
Compounds of the formula I where (X)m is 4-chloro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 173
Compounds of the formula I where (X)m is 5-chloro, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 174
Compounds of the formula I where (X)m is 5-chloro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 175
Compounds of the formula I where (X)m is 5-chloro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 176
Compounds of the formula I where (X)m is 5-chloro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 177
Compounds of the formula I where (X)m is 3-bromo, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 178
Compounds of the formula I where (X)m is 3-bromo, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 179
Compounds of the formula I where (X)m is 3-bromo, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 180
Compounds of the formula I where (X)m is 3-bromo, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 181
Compounds of the formula I where (X)m is 4-bromo, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 182
Compounds of the formula I where (X)m is 4-bromo, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 183
Compounds of the formula I where (X)m is 4-bromo, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 184
Compounds of the formula I where (X)m is 4-bromo, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 185
Compounds of the formula I where (X)m is 5-bromo, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 186
Compounds of the formula I where (X)m is 5-bromo, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 187
Compounds of the formula I where (X)m is 5-bromo, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 188
Compounds of the formula I where (X)m is 5-bromo, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 189
Compounds of the formula I where (X)m is 3-nitro, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 190
Compounds of the formula I where (X)m is 3-nitro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 191
Compounds of the formula I where (X)m is 3-nitro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 192
Compounds of the formula I where (X)m is 3-nitro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 193
Compounds of the formula I where (X)m is 4-nitro, A and R2 are hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 194
Compounds of the formula I where (X)m is 4-nitro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 195
Compounds of the formula I where (X)m is 4-nitro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 196
Compounds of the formula I where (X)m is 4-nitro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
Table 197
Compounds of the formula I where (X)m is 5-nitro, A is hydroxyl and R2 is hydrogen, and the radical R1 for each compound corresponds to one line of Table A
Table 198
Compounds of the formula I where (X)m is 5-nitro, A is hydroxyl and R2 is methyl, and the radical R1 for each compound corresponds to one line of Table A
Table 199
Compounds of the formula I where (X)m is 5-nitro, A is hydroxyl and R2 is methoxy, and the radical R1 for each compound corresponds to one line of Table A
Table 200
Compounds of the formula I where (X)m is 5-nitro, A is hydroxyl and R2 is cyano, and the radical R1 for each compound corresponds to one line of Table A
The compounds I are suitable as fungicides. They are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them act systemically, and they can be employed in crop protection as foliar- and soil-acting fungicides.
They are especially important for controlling a large number of fungi on a variety of crop plants such as wheat, rye, barley, oats, rice, maize, grass, bananas, cotton, soybean, coffee, sugar cane, grapevine, fruit species, ornamentals and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.
Specifically, they are suitable for controlling the following plant diseases:
Alternaria species on vegetables and fruit,
Botrytis cinerea (gray mold) on strawberries, vegetables, ornamentals and grapevines,
Cercospora arachidicola on peanuts,
Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits,
Erysiphe graminis (powdery mildew) on cereals,
Fusarium- and Verticillium species on a variety of plants,
Helminthosporium species on cereals,
Mycosphaerella species on bananas and peanuts,
Phytophthora infestans on potatoes and tomatoes,
Plasmopara viticola on grapevines,
Podosphaera leucotricha on apples,
Pseudocercosporella herpotrichoides on wheat and barley,
Pseudoperonospora species on hops and cucumbers,
Puccinia species on cereals,
Pyricularia oryzae on rice,
Rhizoctonia species on cotton, rice and turf,
Septoria nodorum on wheat,
Uncinula necator on grapevines,
Ustilago species on cereals and sugar cane, and
Venturia species (scab) on apples and pears.
Moreover, the compounds I are suitable for controlling harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, paint dispersions, fibers and fabrics) and in the protection of stored products.
The compounds I are applied by treating the fungi, or the plants, seed, materials or the soil to be protected against fungal infection, with a fungicidally active amount of the active ingredients. Application can be effected both before and after infection of the materials, plants or seeds by the fungi.
In general, the fungicidal compositions comprise from 0.1 to 95, preferably 0.5 to 90, % by weight of active ingredient.
When used in crop protection, the application rates are from 0.01 to 2.0 kg of active ingredient per ha, depending on the nature of the desired effect.
In the treatment of seeds, amounts of active ingredient of from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.
When used in the protection of materials or stored products, the application rate of active ingredient depends on the nature of the field of application and on the desired effect. Application rates conventionally used in the protection of materials are, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active ingredient per cubic meter of material treated.
The compounds I can be converted into the customary formulations, e.g. solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular purpose; it is intended to ensure in each case a fine and uniform distribution of the compound according to the invention.
The formulations are prepared in a known manner, e.g. by extending the active ingredient with solvents and/or carriers, if desired using emulsifiers and dispersants, it also being possible to use other organic solvents as cosolvents if water is used as the diluent. Auxiliaries which are suitable are essentially: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanones), amines (e.g. ethanolamine, N,N-dimethylformamide) and water; carriers such as ground natural minerals (e.g. kaolins, clays, talc, chalk) and ground synthetic minerals (e.g. highly disperse silica, silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali metal and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ether, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol or formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dusts can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, e.g. coated granules, impregnated granules, homogeneous granules, can be prepared by binding the active ingredients on solid carriers. Examples of solid carriers are mineral earths such as silicas, silica gels, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In general, the formulations comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient. The active ingredients are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
The following are examples of formulations:
I. 5 parts by weight of a compound according to the invention are mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust which comprises 5% by weight of the active ingredient.
II. 30 parts by weight of a compound according to the invention are mixed intimately with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of paraffin oil which had been sprayed onto the surface of this silica gel. This gives a formulation of active ingredient with good adhesion properties (active ingredient content 23% by weight).
III. 10 parts by weight of a compound according to the invention are dissolved in a mixture composed of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts by weight of calcium dodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (active ingredient compound 9% by weight).
IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 5 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil (active ingredient content 16% by weight).
V. 80 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill (active ingredient content 80% by weight).
VI. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-xcex1-pyrrolidone, which gives a solution which is suitable for use in the form of microdrops (active ingredient content 90% by weight).
VII. 20 parts by weight of a compound according to the invention are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion comprising 0.02% by weight of the active ingredient.
VIII. 20 parts by weight of a compound according to the invention are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalene-xcex1-sulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture comprising 0.1% by weight of the active ingredient.
The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; it is intended to ensure in each case the finest possible distribution of the active ingredients according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
The active ingredient concentrations in the ready-to-use products can be varied within relatively wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
The active ingredients may also be used successfully in the ultra-low-volume method (ULV), it being possible to apply formulations comprising over 95% by weight of active ingredient, or even to apply the active ingredient without additives.
Various types of oils, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate immediately prior to use (tank mix). These agents can be admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.
In the use form as fungicides, the compositions according to the invention can also be present together with other active ingredients, e.g. with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides frequently results in a broader fungicidal spectrum of action.
The following list of fungicides together with which the compounds according to the invention can be used is intended to illustrate the possible combinations, but not to impose any limitation:
sulfur, dithiocarbamates and their derivatives, such as iron(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate, manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuram disulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate), ammonia complex of zinc (N,Nxe2x80x2-propylenebisdithiocarbamate), zinc (N,Nxe2x80x2-propylenebisdithiocarbamate), N,Nxe2x80x2-polypropylenebis(thiocarbamoyl) disulfide;
nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl 5-nitro-isophthalate;
heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl phthalimidophosphonothioate, 5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-dithioanthraquinone, 2-thio-1,3-dithiolo[4,5-b]-quinoxaline, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamate, 2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)benzimidazole, 2-(4-thiazolyl)benzimidazole, N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide, N-trichloromethylthiotetrahydrophthalimide, N-trichloromethylthiophthalimide;
N-dichlorofluoromethylthio-Nxe2x80x2,Nxe2x80x2-dimethyl-N-phenylsulfodiamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol 1-oxide, 8-hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine, 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide, 2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide, 2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl-2,5-dimethylfuran-3-carboxamide, N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide, 2-methylbenzanilide, 2-iodobenzanilide, N-formyl-N-morpholine-2,2,2-trichloroethyl acetal, piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide, 1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane;
amines such as 2,6-dimethyl-N-tridecylmorpholine or its salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts, N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine, N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine;
azoles such as 1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole, N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-Nxe2x80x2-imidazolylurea, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol, (2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole, xcex1-(2-chlorophenyl)-xcex1-(4-chlorophenyl)-5-pyrimidinemethanol, 5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine, bis(p-chlorophenyl)-3-pyridinemethanol, 1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene, 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene;
strobilurins such as methyl E-methoxyimino-[xcex1-(o-tolyloxy)-o-tolyl]acetate, methyl E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate, N-methyl-E-methoxy imino-[xcex1-(2-phenoxyphenyl)]acetamide, N-methyl E-methoxyimino-[xcex1-(2,5-dimethylphenoxy)-o-tolyl]acetamide; methyl E-2-{2-[2-trifluoromethylpyridyl-6-]oxymethyl]phenyl}-3-methoxyacrylate, methyl (E,E)-methoximino-{2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}acetate, methyl N-(2-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]-oxymethyl}phenyl)N-methoxycarbamate,
anilinopyrimidines such as N-(4,6-dimethylpyrimidin-2-yl)aniline, N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline, N-[4-methyl-6-cyclopropylpyrimidin-2-yl]aniline;
phenylpyrroles such as 4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole-3-carbonitrile;
cinnamamides such as 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloylmorpholine;
and a variety of fungicides such as dodecylguanidine acetate, 3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide, hexachlorobenzene, methyl N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninate, DL-N-(2,6-dimethylphenyl)-N-(2xe2x80x2-methoxyacetyl)alanine methyl ester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-amino-butyrolactone, DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester, 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine, 3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide, 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole, 2,4-difluoro-xcex1-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol, N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine, 1-((bis(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.